Brasiliquinone C
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| Category | Antibiotics |
| Catalog number | BBF-00176 |
| CAS | 183201-06-1 |
| Molecular Weight | 350.36 |
| Molecular Formula | C21H18O5 |
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Description
Brasiliquinone C is a benzo-onionquinone antibiotic produced by Nocardia brasiliensis, which has anti-gram-positive bacteria and tumor activity.
Specification
| Synonyms | (3S)-3-ethyl-6-hydroxy-8-methoxy-3,4-dihydrotetraphene-1,7,12(2H)-trione |
| IUPAC Name | (3S)-3-ethyl-6-hydroxy-8-methoxy-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CCC1CC2=CC(=C3C(=C2C(=O)C1)C(=O)C4=C(C3=O)C(=CC=C4)OC)O |
| InChI | InChI=1S/C21H18O5/c1-3-10-7-11-9-14(23)18-19(16(11)13(22)8-10)20(24)12-5-4-6-15(26-2)17(12)21(18)25/h4-6,9-10,23H,3,7-8H2,1-2H3/t10-/m0/s1 |
| InChI Key | JCMDNBJXOUWFMR-JTQLQIEISA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Melting Point | 215-217°C |
| Solubility | Soluble in Methanol, chloroform, ethyl acetate, methyl ether |
Reference Reading
1. Brasiliquinones A, B and C, new benz[alpha]anthraquinone antibiotics from Nocardia brasiliensis. I. Producing strain, isolation and biological activities of the antibiotics
A Nemoto, Y Tanaka, Y Karasaki, H Komaki, K Yazawa, Y Mikami, T Tojo, K Kadowaki, M Tsuda, J Kobayashi J Antibiot (Tokyo). 1997 Jan;50(1):18-21. doi: 10.7164/antibiotics.50.18.
New benz[alpha]anthraquinone antibiotics (brasiliquinones A, B and C) with an ethyl group at C-3 were isolated. The producer was identified as Nocardia brasiliensis. The antibiotics were active against Gram-positive bacteria including Mycobacterium sp., but not active against Gram-negative bacteria or fungi. They were also active against multiple drug-resistant P388/ADR tumor cells.
2. Asymmetric Total Synthesis of Brasiliquinones B and C via Oxidative Cyclization of a Hydroquinone-Silyl Enol Ether Hybrid
Hiroki Miyake, Ryo Nakajima, Takuya Kumamoto J Org Chem. 2022 Sep 16;87(18):12491-12497. doi: 10.1021/acs.joc.2c01653. Epub 2022 Aug 30.
The asymmetric total synthesis of angucycline antibiotics (S)-brasiliquinones B and C was accomplished. The benz[a]anthraquinone core was constructed via oxidative cyclization of a hydroquinone-silyl enol ether hybrid. The resultant pentacyclic acetal was converted to the silyl enol ether, which was treated with Pd(II)/O2 to afford brasiliquinone C, after multistep conversion including dehydrogenation, desilylation and deacetalization, and hydroquinone oxidation. The (S)-configuration of natural brasiliquinones was confirmed based on the stereochemical correlation with the synthetic products.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
